Potassium Carbonate → 3-[3-(Hydroxymethyl)benzylthio]benzaldehyde

HRID 2254476Notes

Reaction equation

HRID 2254476 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[OH:10][CH2:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:10][CH2:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][S:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 149468343-SulfanylbenzaldehydeHCID 19032333(3-(Bromomethyl)phenyl)methanol

Product 1

HCID 197446443-[3-(Hydroxymethyl)benzylthio]benzaldehydeYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 mg of 3-mercaptobenzaldehyde was dissolved in 6 ml of dimethylformamide, and 291 mg of 3-hydroxymethylbenzyl bromide and 402 mg of potassium carbonate were added. The mixture was stirred for 3 hours at room temperature. The solvent was evaporated, water and ethyl ether were added to the residue to extract it. The extract was worked up in a customary manner, and purified by silica gel column chromatography [Wakogel C-200, 10 g; eluting solvent: hexane/ethyl acetate=2/1] to give 190 mg (yield 51%) of 3-[3-(hydroxymethyl)benzylthio]benzaldehyde as a pale yellow oil.

Workup

  1. customThe solvent was evaporated
  2. additionwater and ethyl ether were added to the residue
  3. extractionto extract it
  4. custompurified by silica gel column chromatography [Wakogel C-200, 10 g; eluting solvent: hexane/ethyl acetate=2/1]

Sources & evidence

ORD record
ord-a4446670440348fe8319cf2be265b890
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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